Search Deals onCheshire Vacation Packages
Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was $729, price is now $592 per person
$592
per person
Jul 6 - Jul 11
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
The Yankee Inn
Save 100% on your flight
Price was $1,205, price is now $887 per person
$887
per person
Jun 26 - Jun 30
just found
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was $920, price is now $691 per person
$691
per person
Jun 26 - Jun 30
just found
Roundtrip non-stop flight included
Baltimore (BWI) to Albany (ALB)
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Cheshire Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Cheshire Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Jun 9 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Wed, May 27 - Sat, May 30
CLT
Charlotte-Douglas Intl.
ALB
Albany Intl.
$253 Roundtrip, found 5 days ago
$253
Roundtrip
found 5 days ago
Sat, Jun 27 - Sat, Jul 11
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Sat, Aug 29 - Sun, Sep 6
TPA
Tampa Intl.
ALB
Albany Intl.
$328 Roundtrip, found 19 hours ago
$328
Roundtrip
found 19 hours ago
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